NPASS Compound

Natural Product: NPC30397

Natural Product ID	NPC30397
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-Glucopyranosyl Quinovic Acid28-O-Beta-D-Glucopyranosyl Ester
IUPAC Name	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL501302
PubChem CID	14194010
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 123129 0 0 0 0 0 0 0 0999 V2000 10.5145 2.4397 2.8944 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3181 2.5512 2.2227 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8958 1.1913 1.6486 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7064 1.4138 1.0066 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1501 0.2614 0.4149 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0217 0.7372 -0.2491 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8233 0.1990 0.2247 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0068 1.2249 0.9660 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5637 0.9173 1.0970 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9331 0.6487 -0.2494 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6289 -0.5156 -0.8480 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1089 -0.5511 -0.8287 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5965 -1.9923 -0.7775 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6165 -0.0426 -2.1890 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0455 -0.6974 -2.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6005 -1.0066 -2.2276 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2227 -0.3128 -1.1928 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5070 0.1982 -0.0187 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3371 1.1194 0.8001 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6184 0.4009 1.0563 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0555 -0.6664 0.4023 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2805 -1.3092 -0.7241 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2162 -1.5604 -1.9032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6427 -1.3262 -1.6764 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2145 -1.7227 -0.3263 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3744 -1.2359 0.8103 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1626 -2.2627 1.9098 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8145 -1.5127 3.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4156 -3.0468 2.1870 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0574 -4.1725 3.1358 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0247 -3.6485 0.9705 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5200 -3.1862 -0.3372 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5544 -1.0394 -0.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6011 -1.6765 -0.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6439 0.3493 -0.3737 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8561 1.0614 -0.3672 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9596 1.7818 -1.5315 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1487 2.4460 -1.7015 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.8824 3.6286 -2.6305 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0232 4.3716 -2.8702 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7545 2.9476 -0.4102 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7062 3.1666 0.6539 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8440 1.9542 0.8769 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3321 1.1538 1.9171 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9056 4.2611 0.4098 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6572 1.9944 0.0293 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7000 -2.6180 -0.3391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0048 -3.6873 -0.9908 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1749 -2.8884 0.6781 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0182 0.8393 -1.8271 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9666 1.9021 -1.0417 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1464 -0.2534 -0.5692 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5384 -0.4061 -0.0569 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9727 0.8632 0.6056 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1868 0.6943 1.2298 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3756 -0.5873 -1.1808 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7711 -1.4506 -1.1644 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2229 3.0446 2.5319 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5097 3.0218 2.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5052 3.2161 1.3323 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8704 0.4211 2.4293 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8592 -0.4685 1.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1647 -0.5095 1.0420 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2261 2.2142 0.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3881 1.3516 2.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4199 0.0308 1.7229 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0610 1.8272 1.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2740 -1.4359 -0.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7143 -2.6698 -0.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2403 -2.1792 0.1203 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1752 -2.2938 -1.6532 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1688 0.9018 -2.4846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5334 -0.8431 -2.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7020 0.1365 -2.0512 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3487 0.1141 -2.9416 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5856 -1.6078 -2.6523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1825 -0.7086 -3.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4416 -2.1265 -2.2111 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6660 -0.6764 0.6872 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4479 2.1363 0.4488 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1498 1.1990 1.8186 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2249 0.8318 1.8723 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0780 -2.6215 -2.2782 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9140 -0.9568 -2.7989 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0284 -0.3164 -1.9160 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2193 -1.9786 -2.4078 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9802 -0.4295 1.3292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3640 -2.9688 1.7083 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9685 -2.1443 4.0800 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4983 -0.6371 3.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7558 -1.1856 3.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1299 -2.3843 2.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0842 -3.8474 4.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7339 -5.0250 2.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0344 -4.5241 2.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9296 -4.7773 0.9688 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1336 -3.4977 1.0298 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7145 -3.8097 -0.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3772 -3.3069 -1.0749 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7358 0.3547 -0.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9128 1.8187 -2.2155 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0939 4.2476 -2.1126 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4432 3.2092 -3.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7220 5.3288 -2.9573 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2348 3.9323 -0.5921 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2492 3.3549 1.6066 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7889 2.2330 1.0498 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0910 1.5955 2.7695 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4138 5.0692 0.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1633 2.3118 0.8075 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7701 -3.6837 0.7527 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6230 1.8363 -1.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9212 0.7966 -2.9311 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0503 0.8635 -1.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3375 2.6587 -0.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9677 2.3963 -1.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6828 1.8351 -2.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1857 0.5016 -1.4071 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6757 -1.2638 0.6204 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9681 1.6888 -0.1392 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8408 0.4289 0.5103 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0315 -1.3211 -1.0211 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5694 -2.0522 -1.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 11 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 25 33 1 1 33 34 2 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 41 46 1 0 22 47 1 1 47 48 2 0 47 49 1 0 17 50 1 6 10 51 1 6 5 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 54 3 1 0 12 7 1 0 22 17 1 0 32 25 1 0 43 36 1 0 18 10 1 0 26 21 1 0 1 58 1 0 2 59 1 0 2 60 1 0 3 61 1 1 5 62 1 1 7 63 1 1 8 64 1 0 8 65 1 0 9 66 1 0 9 67 1 0 11 68 1 1 13 69 1 0 13 70 1 0 13 71 1 0 14 72 1 0 14 73 1 0 14 74 1 0 15 75 1 0 15 76 1 0 16 77 1 0 16 78 1 0 18 79 1 1 19 80 1 0 19 81 1 0 20 82 1 0 23 83 1 0 23 84 1 0 24 85 1 0 24 86 1 0 26 87 1 1 27 88 1 6 28 89 1 0 28 90 1 0 28 91 1 0 29 92 1 1 30 93 1 0 30 94 1 0 30 95 1 0 31 96 1 0 31 97 1 0 32 98 1 0 32 99 1 0 36100 1 1 38101 1 6 39102 1 0 39103 1 0 40104 1 0 41105 1 6 42106 1 1 43107 1 1 44108 1 0 45109 1 0 46110 1 0 49111 1 0 50112 1 0 50113 1 0 50114 1 0 51115 1 0 51116 1 0 51117 1 0 52118 1 6 53119 1 1 54120 1 6 55121 1 0 56122 1 0 57123 1 0 M END

Standard InCHIKey	LDCLXZSKVDYDBF-DTJUAWDLSA-N
Standard InCHI	InChI=1S/C42H66O15/c1-19-9-14-41(37(53)57-35-33(50)31(48)29(46)23(18-44)55-35)15-16-42(36(51)52)21(27(41)20(19)2)7-8-25-39(5)12-11-26(38(3,4)24(39)10-13-40(25,42)6)56-34-32(49)30(47)28(45)22(17-43)54-34/h7,19-20,22-35,43-50H,8-18H2,1-6H3,(H,51,52)/t19-,20+,22-,23-,24+,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,39+,40-,41+,42-/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@]2(CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	810.44	Volume:	799.037 ? Van der Waals volume.
Dense:	1.014	LogP:	0.822 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.961 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.199 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	40.0
TPSA:	253.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	7.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.1	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.916	Fsp³:	0.905
MCE-18:	151.25 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.851	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.029 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.161	Promiscuous compounds:	0.207

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.141	MDCK Permeability:	-5.044
Pgp-inhibitor:	0.0	Pgp-substrate:	0.065
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.781
20% Bioavailability (F20%):	0.255	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.197
Plasma Protein Binding (PPB):	64.623%	Volume Distribution (VD):	-0.512
Fu:	29.713% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.028	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

0.432

Half-life (T1/2):

3.024

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.841	Drug-induced Liver Injury (DILI):	0.977
AMES Toxicity:	0.942	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.419	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.612	Drug-induced Nephrotoxicity:	0.991
Genotoxicity:	0.9	RPMI-8226 Immunitoxicity:	0.05
A549 Cytotoxicity:	0.258	Hek293 Cytotoxicity:	0.103
BCF:	0.581 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.358 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.856 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.95 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22560	Strychnos parvifolia	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22475.1	Brachylaena discolor var. rotundata	Varieties	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22818	Acritopappus confertus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21220	Pulicaria uliginosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	2
MIC50	1
Activity	2
MNCC	1

Activity Type	# Activity
Individual protein	2
Cell line	1
Organism	3

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual protein	DNA topoisomerase II alpha	Homo sapiens	IC50	>	250000.0	nM	PMID[20371180]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	>	250000.0	nM	PMID[20371180]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell line	HeLa	Homo sapiens	MNCC	=	100.0	ug ml-1	PMID[2553871]
NPT2517	Organism	Human rhinovirus 1B	Human rhinovirus 1B	Activity	=	50.0	%	PMID[2553871]
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	MIC50	=	40000.0	nM	PMID[2553871]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC30397 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	16301
0.1-0.2	27552
0.2-0.3	4685
0.3-0.4	1012
0.4-0.5	273
0.5-0.6	23
0.6-0.7	4
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.975	High Similarity	NPC235841
0.975	High Similarity	NPC297208
0.8966	High Similarity	NPC124296
0.8333	Intermediate Similarity	NPC607754
0.7209	Intermediate Similarity	NPC274507
0.6526	Remote Similarity	NPC211798
0.6495	Remote Similarity	NPC108748
0.6421	Remote Similarity	NPC473481
0.6058	Remote Similarity	NPC258885
0.5698	Remote Similarity	NPC60755
0.5698	Remote Similarity	NPC77099
0.5673	Remote Similarity	NPC475171
0.5532	Remote Similarity	NPC484195
0.5361	Remote Similarity	NPC606107
0.5327	Remote Similarity	NPC75417
0.5315	Remote Similarity	NPC114484
0.5283	Remote Similarity	NPC157868
0.5253	Remote Similarity	NPC31839
0.5229	Remote Similarity	NPC40775
0.5229	Remote Similarity	NPC159309
0.5229	Remote Similarity	NPC86222
0.5204	Remote Similarity	NPC57362
0.5185	Remote Similarity	NPC192791
0.5146	Remote Similarity	NPC214484
0.5114	Remote Similarity	NPC473242
0.5114	Remote Similarity	NPC290690
0.5104	Remote Similarity	NPC473844
0.5091	Remote Similarity	NPC251768
0.5048	Remote Similarity	NPC48499
0.5045	Remote Similarity	NPC475591
0.5045	Remote Similarity	NPC236870
0.5044	Remote Similarity	NPC281148

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC30397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5433
0.1-0.2	3613
0.2-0.3	95
0.3-0.4	9
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data